5043-03-8Relevant articles and documents
Rational Design of a Two-Photon Fluorogenic Probe for Visualizing Monoamine Oxidase A Activity in Human Glioma Tissues
Fang, Haixiao,Huang, Wei,Li, Lin,Li, Zheng,Ma, Bo,Ni, Yun,Shi, Riri,Wu, Qiong,Yang, Naidi,Yang, Xuekang,Yao, Shao Q.,Yu, Changmin,Zhang, Chengwu,Zhang, Hang
, p. 7536 - 7541 (2020)
Monoamine oxidases have two functionally distinct but structurally similar isoforms (MAO-A and MAO-B). The ability to differentiate them by using fluorescence detection/imaging technology is of significant biological relevance, but highly challenging with available chemical tools. Herein, we report the first MAO-A-specific two-photon fluorogenic probe (F1), capable of selective imaging of endogenous MAO-A enzymatic activities from a variety of biological samples, including MAO-A-expressing neuronal SY-SY5Y cells, the brain of tumor-bearing mice and human Glioma tissues by using two-photon fluorescence microscopy (TPFM) with minimal cytotoxicity.
ICT-based fluorescent ratiometric probe for monitoring mitochondrial peroxynitrite in living cells
Du, Yuting,Wang, Hongliang,Zhang, Ting,Wei, Wen,Guo, Minmin
supporting information, p. 12915 - 12921 (2021/08/03)
Peroxynitrite (ONOO?) is a reactive oxygen species (ROS) that causes serious damage to living cells and is the cause of a series of human diseases. It is reported that mitochondria are the major site of ONOO?production. Therefore, accurate and rapid detection of intracellular ONOO?is important in pathological processes. Herein, a mitochondria-targeted ratiometric fluorescent probe (DMANI) has been rationally designed based on the coumarin-hemicyanine hybrid framework by regulating the intramolecular charge transfer (ICT) effect. TheDMANIcan capture ONOO?at low concentrationsviadirect addition with the CC bond to give an obvious fluorescent signal change from red to blue based on the ICT process. The possible mechanism for this electrophilic addition process was confirmed using electrospray ionization mass spectrometry (ESI-MS) and1H-NMR spectra.DMANIexhibited a good selectivity, a large Stokes shift (248 nm), a low detection limit (40 nM), and a rapid response (within 20 s) to ONOO?. More importantly,DMANIwas successfully used for ratiometric imaging and monitoring of the fluctuations of mitochondrial ONOO?in living cells.
DANPY (dimethylaminonaphthylpyridinium): an economical and biocompatible fluorophore
Johnson, Lewis E.,Kingsbury, Jason S.,Elder, Delwin L.,Cattolico, Rose Ann,Latimer, Luke N.,Hardin, William,De Meulenaere, Evelien,Deodato, Chloe,Depotter, Griet,Madabushi, Sowmya,Bigelow, Nicholas W.,Smolarski, Brittany A.,Hougen, Trevor K.,Kaminsky, Werner,Clays, Koen,Robinson, Bruce H.
supporting information, p. 3765 - 3780 (2019/04/16)
Dyes with nonlinear optical (NLO) properties enable new imaging techniques and photonic systems. We have developed a dye (DANPY-1) for photonics applications in biological substrates such as nucleic acids; however, the design specification also enables it to be used for visualizing biomolecules. It is a prototype dye demonstrating a water-soluble, NLO-active fluorophore with high photostability, a large Stokes shift, and a favorable toxicity profile. A practical and scalable synthetic route to DANPY salts has been optimized featuring: (1) convergent Pd-catalyzed Suzuki coupling with pyridine 4-boronic acid, (2) site-selective pyridyl N-methylation, and (3) direct recovery of crystalline intermediates without chromatography. We characterize the optical properties, biocompatibility, and biological staining behavior of DANPY-1. In addition to stability and solubility across a range of polar media, the DANPY-1 chromophore shows a first hyperpolarizability similar to common NLO dyes such as Disperse Red 1 and DAST, a large two-photon absorption cross section for its size, substantial affinity to nucleic acids in vitro, an ability to stain a variety of cellular components, and strong sensitivity of its fluorescence properties to its dielectric environment.
